2-[(2R,4aS,6R,8S,8aR)-6,8-dihydroxy-4a,8-dimethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoic acid

Details

• Internal ID: 37fc28e5-0ef8-40a7-ba7c-6c73a591cd7a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2R,4aS,6R,8S,8aR)-6,8-dihydroxy-4a,8-dimethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC12CCC(CC1C(CC(C2)O)(C)O)C(=C)C(=O)O
• SMILES (Isomeric): C[C@@]12CC[C@H](C[C@H]1[C@@](C[C@@H](C2)O)(C)O)C(=C)C(=O)O
• InChI: InChI=1S/C15H24O4/c1-9(13(17)18)10-4-5-14(2)7-11(16)8-15(3,19)12(14)6-10/h10-12,16,19H,1,4-8H2,2-3H3,(H,17,18)/t10-,11-,12-,14+,15+/m1/s1
• InChI Key: ZVJCVPQIEVSWAD-FPVZYODXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₄
• Molecular Weight: 268.35 g/mol
• Exact Mass: 268.16745924 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 1.96
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9832	98.32%
Caco-2	+	0.5708	57.08%
Blood Brain Barrier	-	0.5473	54.73%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6849	68.49%
OATP2B1 inhibitior	-	0.8517	85.17%
OATP1B1 inhibitior	+	0.9204	92.04%
OATP1B3 inhibitior	-	0.2740	27.40%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6827	68.27%
BSEP inhibitior	-	0.9402	94.02%
P-glycoprotein inhibitior	-	0.9292	92.92%
P-glycoprotein substrate	-	0.8090	80.90%
CYP3A4 substrate	+	0.6011	60.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8918	89.18%
CYP3A4 inhibition	-	0.7218	72.18%
CYP2C9 inhibition	-	0.8130	81.30%
CYP2C19 inhibition	-	0.8918	89.18%
CYP2D6 inhibition	-	0.9349	93.49%
CYP1A2 inhibition	-	0.8215	82.15%
CYP2C8 inhibition	-	0.8218	82.18%
CYP inhibitory promiscuity	-	0.9473	94.73%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6111	61.11%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.7780	77.80%
Skin irritation	+	0.5147	51.47%
Skin corrosion	-	0.9388	93.88%
Ames mutagenesis	-	0.5937	59.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6125	61.25%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.6467	64.67%
skin sensitisation	-	0.6305	63.05%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.8612	86.12%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	I	0.4515	45.15%
Estrogen receptor binding	+	0.8572	85.72%
Androgen receptor binding	-	0.5800	58.00%
Thyroid receptor binding	+	0.5473	54.73%
Glucocorticoid receptor binding	+	0.7310	73.10%
Aromatase binding	+	0.6078	60.78%
PPAR gamma	+	0.6097	60.97%
Honey bee toxicity	-	0.8731	87.31%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9933	99.33%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.06%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	93.35%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.66%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.61%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	84.79%	91.19%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.56%	82.69%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.49%	96.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.96%	100.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.15%	96.38%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.94%	91.11%
CHEMBL284	P27487	Dipeptidyl peptidase IV	80.18%	95.69%

Plants that contains it

• Dittrichia graveolens

Cross-Links

• PubChem: 25130456
• LOTUS: LTS0198290
• wikiData: Q105384338